JP2019530667A5 - - Google Patents
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- Publication number
- JP2019530667A5 JP2019530667A5 JP2019513033A JP2019513033A JP2019530667A5 JP 2019530667 A5 JP2019530667 A5 JP 2019530667A5 JP 2019513033 A JP2019513033 A JP 2019513033A JP 2019513033 A JP2019513033 A JP 2019513033A JP 2019530667 A5 JP2019530667 A5 JP 2019530667A5
- Authority
- JP
- Japan
- Prior art keywords
- isopropyl
- piperidine
- indole
- indol
- dimethylpyridine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 2 -cyclopropyl Chemical group 0.000 claims 714
- IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 155
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 55
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 42
- 125000000217 alkyl group Chemical group 0.000 claims 41
- 125000002496 methyl group Chemical compound [H]C([H])([H])* 0.000 claims 37
- 150000003869 acetamides Chemical compound 0.000 claims 26
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 23
- DLFVBJFMPXGRIB-UHFFFAOYSA-N acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 20
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 18
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-Aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 13
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 12
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-Lutidine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims 11
- 125000003277 amino group Chemical compound 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 10
- 125000004482 piperidin-4-yl group Chemical compound N1CCC(CC1)* 0.000 claims 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 9
- NBBJYMSMWIIQGU-UHFFFAOYSA-N propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims 9
- HNJBEVLQSNELDL-UHFFFAOYSA-N 2-Pyrrolidone Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000002883 imidazolyl group Chemical group 0.000 claims 8
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000011780 sodium chloride Substances 0.000 claims 8
- 125000000335 thiazolyl group Chemical group 0.000 claims 8
- 125000001425 triazolyl group Chemical group 0.000 claims 8
- 150000001204 N-oxides Chemical class 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 7
- FVSKHRXBFJPNKK-UHFFFAOYSA-N Propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 125000002757 morpholinyl group Chemical group 0.000 claims 6
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 6
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims 5
- 125000002971 oxazolyl group Chemical group 0.000 claims 5
- 125000003566 oxetanyl group Chemical group 0.000 claims 5
- 125000004193 piperazinyl group Chemical group 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 5
- WNVZOHNNPDZYFN-UHFFFAOYSA-N 1,2-oxazole-3-carbaldehyde Chemical compound O=CC=1C=CON=1 WNVZOHNNPDZYFN-UHFFFAOYSA-N 0.000 claims 4
- QDVBKXJMLILLLB-UHFFFAOYSA-N 1,4'-bipiperidine Chemical compound C1CCCCN1C1CCNCC1 QDVBKXJMLILLLB-UHFFFAOYSA-N 0.000 claims 4
- RQEDXUKWSYJDPG-UHFFFAOYSA-N 1-piperidin-4-ylindole Chemical compound C1CNCCC1N1C2=CC=CC=C2C=C1 RQEDXUKWSYJDPG-UHFFFAOYSA-N 0.000 claims 4
- 125000004778 2,2-difluoroethyl group Chemical compound [H]C([H])(*)C([H])(F)F 0.000 claims 4
- DUQGFIKXKISULR-UHFFFAOYSA-N 3-methyloxetane-3-carbaldehyde Chemical compound O=CC1(C)COC1 DUQGFIKXKISULR-UHFFFAOYSA-N 0.000 claims 4
- KHLXCSHZEYMJNN-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(CC#N)=O)C1=CC(=NC=C1)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(CC#N)=O)C1=CC(=NC=C1)C KHLXCSHZEYMJNN-UHFFFAOYSA-N 0.000 claims 4
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
- AOSVDOPPFPPBPS-UHFFFAOYSA-N CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC1(CCC1)C)=O)C Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(CNC1(CCC1)C)=O)C AOSVDOPPFPPBPS-UHFFFAOYSA-N 0.000 claims 4
- HINPDWKQQUCHCX-UHFFFAOYSA-N CC1=NC(=CC(=C1)C=1NC2=CC=CC=C2C=1C(C)C)C Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=CC=C2C=1C(C)C)C HINPDWKQQUCHCX-UHFFFAOYSA-N 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 4
- HRVXPXCISZSDCC-UHFFFAOYSA-N piperidine-4-carbaldehyde Chemical compound O=CC1CCNCC1 HRVXPXCISZSDCC-UHFFFAOYSA-N 0.000 claims 4
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000000472 sulfonyl group Chemical compound *S(*)(=O)=O 0.000 claims 4
- 150000003557 thiazoles Chemical compound 0.000 claims 4
- HFBYLYCMISIEMM-FFHNEAJVSA-N (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid Chemical compound OP(O)(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC HFBYLYCMISIEMM-FFHNEAJVSA-N 0.000 claims 3
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-Methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- RXTSZQDKKBHOAC-UHFFFAOYSA-N CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(=O)C1CC(N(C1)C)=O)C Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(=O)C1CC(N(C1)C)=O)C RXTSZQDKKBHOAC-UHFFFAOYSA-N 0.000 claims 3
- 102100005620 DPYS Human genes 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000003725 azepanyl group Chemical group 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 108091022040 dihydropyrimidinase Proteins 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical compound [H]OC([H])([H])* 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 3
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical compound FC(F)(F)* 0.000 claims 3
- ASZLNPRMVCGYCI-UHFFFAOYSA-N 1$l^{2}-azolidine Chemical group C1CC[N]C1 ASZLNPRMVCGYCI-UHFFFAOYSA-N 0.000 claims 2
- HMTUBXVXHHITGO-UHFFFAOYSA-N 1,3,5-trimethylpyrazole-4-carbaldehyde Chemical compound CC1=NN(C)C(C)=C1C=O HMTUBXVXHHITGO-UHFFFAOYSA-N 0.000 claims 2
- KQMBHBNTRKZGBE-UHFFFAOYSA-N 1-(2-methylpropyl)-4-piperidin-1-ylpiperidine Chemical compound C1CN(CC(C)C)CCC1N1CCCCC1 KQMBHBNTRKZGBE-UHFFFAOYSA-N 0.000 claims 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 1-butanal Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims 2
- LKIYWJKEOOFVCV-UHFFFAOYSA-N 1-methylpiperidine-4-carbaldehyde Chemical compound CN1CCC(C=O)CC1 LKIYWJKEOOFVCV-UHFFFAOYSA-N 0.000 claims 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N 2-Piperidinone Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 2
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 2
- KFXJMCXUMDOSFK-UHFFFAOYSA-N 2-propan-2-yloxane-4-carbaldehyde Chemical compound CC(C)C1CC(C=O)CCO1 KFXJMCXUMDOSFK-UHFFFAOYSA-N 0.000 claims 2
- ZGRFBTFRUGAJRA-UHFFFAOYSA-N 3,3-difluoro-1$l^{2}-azolidine Chemical group FC1(F)CC[N]C1 ZGRFBTFRUGAJRA-UHFFFAOYSA-N 0.000 claims 2
- VJQHJNIGWOABDZ-UHFFFAOYSA-N 3-methyloxetane Chemical compound CC1COC1 VJQHJNIGWOABDZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- XILPCSMEKCBYFO-UHFFFAOYSA-N 4-methyl-1,2,4-triazole Chemical compound CN1C=NN=C1 XILPCSMEKCBYFO-UHFFFAOYSA-N 0.000 claims 2
- VXWCTQZREYJEMU-UHFFFAOYSA-N 4-methylpiperidine-4-carbaldehyde Chemical compound O=CC1(C)CCNCC1 VXWCTQZREYJEMU-UHFFFAOYSA-N 0.000 claims 2
- 206010003816 Autoimmune disease Diseases 0.000 claims 2
- CHHBUJKGMOEBSW-UHFFFAOYSA-N C(C(C)C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C Chemical compound C(C(C)C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C CHHBUJKGMOEBSW-UHFFFAOYSA-N 0.000 claims 2
- AWUOQLZOTLZXAZ-UHFFFAOYSA-N C(C(C)C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC=NC=C1)C Chemical compound C(C(C)C)N1CCC(CC1)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC=NC=C1)C AWUOQLZOTLZXAZ-UHFFFAOYSA-N 0.000 claims 2
- WKABIKXMCLQVBM-UHFFFAOYSA-N C(C(C)C)S(=O)(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C Chemical compound C(C(C)C)S(=O)(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C WKABIKXMCLQVBM-UHFFFAOYSA-N 0.000 claims 2
- QDCHKAZDDBXOTA-UHFFFAOYSA-N C(C)(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC(=C1)C)C Chemical compound C(C)(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC(=C1)C)C QDCHKAZDDBXOTA-UHFFFAOYSA-N 0.000 claims 2
- UIONGSXEQHQEDA-UHFFFAOYSA-N C(C)(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC=C1)C Chemical compound C(C)(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CC(=NC=C1)C UIONGSXEQHQEDA-UHFFFAOYSA-N 0.000 claims 2
- FKICZGPUEOWMEX-UHFFFAOYSA-N C(C)(C)(C)N(C(CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C)=O)C Chemical compound C(C)(C)(C)N(C(CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C)=O)C FKICZGPUEOWMEX-UHFFFAOYSA-N 0.000 claims 2
- AYHDGDSWLRHOPX-UHFFFAOYSA-N C(C)(C)(C)N(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C)C Chemical compound C(C)(C)(C)N(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C)C AYHDGDSWLRHOPX-UHFFFAOYSA-N 0.000 claims 2
- HJDLTXZOLZVAJR-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC(=C(C=C12)C1CCN(CC1)CC1CNCC1)C(F)(F)F)C1=CC(=NC=C1)C Chemical compound C(C)(C)C1=C(NC2=CC(=C(C=C12)C1CCN(CC1)CC1CNCC1)C(F)(F)F)C1=CC(=NC=C1)C HJDLTXZOLZVAJR-UHFFFAOYSA-N 0.000 claims 2
- CAJUDZLSXHQKIH-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CC(NCC1)=O)C1=CC(=NC=C1)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CC(NCC1)=O)C1=CC(=NC=C1)C CAJUDZLSXHQKIH-UHFFFAOYSA-N 0.000 claims 2
- AVYLXZDFYNQJKT-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)C1CC(NC1)=O)C1=CC(=NC=C1)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)C1CC(NC1)=O)C1=CC(=NC=C1)C AVYLXZDFYNQJKT-UHFFFAOYSA-N 0.000 claims 2
- KBPBAANPGIPRSG-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)C1CCNCC1)C1=CC(=NC=C1)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)C1CCNCC1)C1=CC(=NC=C1)C KBPBAANPGIPRSG-UHFFFAOYSA-N 0.000 claims 2
- HUYKMKSPPMIHFZ-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C(=O)N(C)C)=O)C1=CC(=NC=C1)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C(=O)N(C)C)=O)C1=CC(=NC=C1)C HUYKMKSPPMIHFZ-UHFFFAOYSA-N 0.000 claims 2
- UWFVLKFCNIYHNT-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C(C#N)(C)C)=O)C1=CC(=NC=C1)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C(C#N)(C)C)=O)C1=CC(=NC=C1)C UWFVLKFCNIYHNT-UHFFFAOYSA-N 0.000 claims 2
- RSCAPQHZLJAENT-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(CCC1CCNCC1)=O)C1=CC(=NC=C1)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(CCC1CCNCC1)=O)C1=CC(=NC=C1)C RSCAPQHZLJAENT-UHFFFAOYSA-N 0.000 claims 2
- JCKVOBRFDMLCNM-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(CCOC)=O)C1=CC(=NC=C1)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(CCOC)=O)C1=CC(=NC=C1)C JCKVOBRFDMLCNM-UHFFFAOYSA-N 0.000 claims 2
- BFJZXMMZBJPLNV-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1C(CNCC1)C)C1=CC(=NC=C1)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1C(CNCC1)C)C1=CC(=NC=C1)C BFJZXMMZBJPLNV-UHFFFAOYSA-N 0.000 claims 2
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- JOHPVHOPKILDIX-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)C)C1=CC(=NC=C1)OC Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)C)C1=CC(=NC=C1)OC JOHPVHOPKILDIX-UHFFFAOYSA-N 0.000 claims 2
- FLTWHXLFOSAIOO-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)C)C1=CC=NC=C1 Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(CC1)C)C1=CC=NC=C1 FLTWHXLFOSAIOO-UHFFFAOYSA-N 0.000 claims 2
- AWTOMRPDGCOZIT-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CC(=NC=C1)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CC(=NC=C1)C AWTOMRPDGCOZIT-UHFFFAOYSA-N 0.000 claims 2
- DGJCLUVWZJLPBW-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC(CNC)=O)C1=CC(=NC=C1)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC(CNC)=O)C1=CC(=NC=C1)C DGJCLUVWZJLPBW-UHFFFAOYSA-N 0.000 claims 2
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Cited By (2)
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| JP7265554B2 (ja) | 2017-11-14 | 2023-04-26 | ブリストル－マイヤーズ スクイブ カンパニー | 置換インドール化合物 |
| JP7382938B2 (ja) | 2017-12-20 | 2023-11-17 | ブリストル－マイヤーズ スクイブ カンパニー | ジアザインドール化合物 |
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| US9643967B2 (en) | 2013-12-13 | 2017-05-09 | Takeda Pharmaceutical Company Limited | Pyrrolo[3,2-c]pyridine derivatives as TLR inhibitors |
| US20170275287A1 (en) | 2014-08-22 | 2017-09-28 | Janus Biotherapeutics, Inc. | Novel n2, n4, n7, 6-tetrasubstituted pteridine-2,4,7-triamine and 2, 4, 6, 7-tetrasubstituted pteridine compounds and methods of synthesis and use thereof |
| GB2534136A (en) * | 2015-01-12 | 2016-07-20 | Nokia Technologies Oy | An apparatus, a method and a computer program for video coding and decoding |
| US10071079B2 (en) | 2016-06-29 | 2018-09-11 | Bristol-Myers Squibb Company | [1,2,4]triazolo[1,5-a]pyridinyl substituted indole compounds |
| CA3031675A1 (fr) | 2016-07-30 | 2018-02-08 | Bristol-Myers Squibb Company | Composes d'indole substitues par du dimethoxyphenyle comme des inhibiteurs de tlr7, tlr8 ou tlr9 |
| KR102519535B1 (ko) | 2016-09-09 | 2023-04-06 | 브리스톨-마이어스 스큅 컴퍼니 | 피리딜 치환된 인돌 화합물 |
-
2017
- 2017-09-08 KR KR1020197009672A patent/KR102519535B1/ko active IP Right Grant
- 2017-09-08 US US16/330,964 patent/US10660877B2/en active Active
- 2017-09-08 WO PCT/US2017/050577 patent/WO2018049089A1/fr unknown
- 2017-09-08 ES ES17768623T patent/ES2902504T3/es active Active
- 2017-09-08 MA MA046188A patent/MA46188A/fr unknown
- 2017-09-08 JP JP2019513033A patent/JP7028861B2/ja active Active
- 2017-09-08 EP EP17768623.5A patent/EP3510024B1/fr active Active
- 2017-09-08 CN CN201780068433.2A patent/CN109923108B/zh active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7265554B2 (ja) | 2017-11-14 | 2023-04-26 | ブリストル－マイヤーズ スクイブ カンパニー | 置換インドール化合物 |
| JP7382938B2 (ja) | 2017-12-20 | 2023-11-17 | ブリストル－マイヤーズ スクイブ カンパニー | ジアザインドール化合物 |
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